JP2014208642A - 架橋可能なイオンドーパント - Google Patents
架橋可能なイオンドーパント Download PDFInfo
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- JP2014208642A JP2014208642A JP2014093435A JP2014093435A JP2014208642A JP 2014208642 A JP2014208642 A JP 2014208642A JP 2014093435 A JP2014093435 A JP 2014093435A JP 2014093435 A JP2014093435 A JP 2014093435A JP 2014208642 A JP2014208642 A JP 2014208642A
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- 101100394073 Caenorhabditis elegans hil-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Chemical group C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical group C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ZTYYDUBWJTUMHW-UHFFFAOYSA-N furo[3,2-b]furan Chemical compound O1C=CC2=C1C=CO2 ZTYYDUBWJTUMHW-UHFFFAOYSA-N 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical compound C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical group C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(1,2−ジヒドロシクロブタベンゼン−4−イル)ジフェニルメタノールの合成
実施例化合物1を用いたデバイスを作製し、比較用化合物を用いたデバイスと比較した。比較用化合物(以下)は、市販の導電ドーパントであり、これは化合物1と異なり、反応性官能基を有していない。
緑色発光OLEDを、化合物1および比較用化合物を用いて作製した。正孔注入材料HIL−1(ホスト材料として)を化合物1または比較用化合物(導電ドーパントとして)と共にシクロヘキサノン溶液中に溶解させた。溶液中の化合物1または比較用化合物の量は、ホスト材料に対して3重量%であった。正孔注入層(HIL)を形成するために、溶液を、パターン形成したインジウムスズ酸化物(ITO)電極上に60秒間4000rpmでスピンコートした。得られたフィルムを250℃で30分間焼成した。フィルムは焼成後不溶性になった。
青色発光OLEDも、化合物1および比較用化合物を用いて作製した。緑色発光ドーパント−1の代りに青色発光ドーパント−2を使用し、ホスト−1の代りにホスト−2を使用したという点を除き、緑色発光デバイスと同じ要領でデバイスを作製した。比較用化合物を用いたデバイスについてのCIE1931の(x,y)色座標は(0.19,0.39)であり、化合物1を用いたデバイスについては(0.19,0.41)であった。したがって、両方のデバイスにおいて色発光は実質的に同じであった。
CBP:4,4’−N,N−ジカルバゾール−ビフェニル
m−MTDATA:4,4’,4’’−トリス(3-メチルフェニルフェニルアミノ)トリフェニルアミン
Alq3:アルミニウム(III)トリス(8−ヒドロキシキノリン)
Bphen:4,7−ジフェニル−1,10−フェナントロリン
n−BPhen:n−ドープBPhen(リチウムでドープ)
F4−TCNQ:テトラフルオロ−テトラシアノ−キノジメタン
p-MTDATA:p−ドープm−MTDATA(F4−TCNQでドープ)
Ir(ppy)3:トリス(2−フェニルピリジン)−イリジウム
Ir(ppz)3:トリス(1−フェニルピラゾロト,N,C(2’)イリジウム(III)
BCP:2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン
TAZ:3−フェニル−4−(1’-ナフチル)−5−フェニル−1,2,4−トリアゾール
CuPc:銅フタロシアニン
ITO:インジウムスズ酸化物
NPD:N,N’−ジフェニル−N−N’−ジ(1−ナフチル)−ベンジジン
TPD:N,N’−ジフェニル−N−N’−ジ(3−トリ)−ベンジジン
BAlq:アルミニウム(III)ビス(2−メチル−8−ヒドロキシキノリナト)4−フェニルフェノレート
mCP:1,3−N,N−ジカルバゾール−ベンゼン
DCM:4−(ジシアノエチレン)−6−(4−ジメチルアミノスチリル−2−メチル)−4H−ピラン
DMQA:N,N’−ジメチルキナクリドン
PEDOT:PSS: ポリ(3,4−エチレンジオキシチオフェン)とポリスチレンスルホネート(PSS)の水性分散
Claims (32)
-
Ar1、Ar2およびAr3は各々互いに独立してアリール基またはヘテロアリール基であり;
Ar1、Ar2およびAr3の少なくとも1つが、ビニル、アクリレート、エポキシド、オキセタン、ノルボルネン、トリフルオロエチレン、ベンゾシクロブテン、シロキサン、マレイミド、シアン酸エステル、エチニル、ナジミド、フェニルエチニル、ビフェニレン、フタロニトリルまたはボロン酸と反応できる反応性官能基を有し;
X1がハロゲンCl、Br、またはIであり;
X2がC、O、SまたはSeであり;
Zn−が、対アニオンであり、「n」はこの対アニオンのイオン価である。)
の式を有するイオン性化合物。 - 前記反応性官能基がビニル、シロキサンまたはボロン酸と反応できる、請求項1に記載のイオン性化合物。
- 前記反応基がビニル含有基、アクリレート含有基、エポキシド含有基、オキセタン含有基、ノルボルネン含有基、トリフルオロエチレン含有基、縮合シクロブテン含有基、シロキサン含有基、マレイミド含有基、シアン酸エステル含有基、エチニル含有基、ナジミド含有基、フェニルエチニル含有基、ビフェニレン含有基、フタロニトリル含有基、またはボロン酸含有基である、請求項1に記載のイオン性化合物。
- 前記反応性官能基がビニル含有基、アクリレート含有基、エポキシド含有基、ノルボルネン含有基、トリフルオロエチレン含有基、または縮合シクロブテン含有基である、請求項1に記載のイオン性化合物。
- 前記反応性官能基が縮合シクロブテン含有基である、請求項4に記載のイオン性化合物。
- Ar1、Ar2およびAr3が各々互いに独立して1〜5個の環を有する、請求項1に記載のイオン性化合物。
- Zn−が
Bはホウ素であり、Ar11〜Ar14が各々互いに独立してアリール基又はヘテロアリール基であり;
Ar11〜Ar14が各々互いに独立して、FまたはClで任意選択により置換されていてもよい。)
の式を有する、請求項1に記載のイオン性化合物。 - Zn−が100〜4,000の範囲内の分子量を有する、請求項7に記載のイオン性化合物。
- Zn−が、
- 前記イオン性化合物のカチオンが、
- 前記イオン性化合物がシクロヘキサノン中で少なくとも1mg/mlの溶解度を有する、請求項1に記載のイオン性化合物。
- 前記イオン性化合物が電子受容体である、請求項1に記載のイオン性化合物。
- 第1の電極と;
前記第1の電極上に配置された第2の電極と;及び
前記第1の電極および前記第2の電極の間に配置された有機層、
を含む電子デバイスであって、
前記有機層が、下記式
Ar1、Ar2およびAr3は各々互いに独立してアリール基またはヘテロアリール基であり;
Ar1、Ar2およびAr3の少なくとも1つが、ビニル、アクリレート、エポキシド、オキセタン、ノルボルネン、トリフルオロエチレン、ベンゾシクロブテン、シロキサン、マレイミド、シアン酸エステル、エチニル、ナジミド、フェニルエチニル、ビフェニレン、フタロニトリルまたはボロン酸と反応できる反応性官能基を有し;
X1がハロゲンCl、Br、またはIであり;
X2がC、O、SまたはSeであり;
Zn−が、対アニオンであり、「n」はこの対アニオンのイオン価である。)
を有するイオン性化合物を用いて作製されている、有機デバイス。 - 前記有機層が、架橋可能な官能基を有するホスト電荷輸送化合物に前記イオン性化合物を架橋させることによって作製される、請求項13に記載の電子デバイス。
- 前記有機層が正孔注入層である、請求項14に記載の電子デバイス。
- 前記イオン性化合物が前記有機層内でp型ドーパントとして機能する、請求項14に記載の電子デバイス。
- 前記ホスト電荷輸送化合物が小分子である、請求項14に記載の電子デバイス。
- 前記ホスト電荷輸送化合物が金属錯体である、請求項14に記載の電子デバイス。
- 前記ホスト電荷輸送化合物がイリジウム錯体である、請求項18に記載の電子デバイス。
- 前記イリジウム錯体が下記式を有する、請求項19に記載の電子デバイス。
Lはイリジウムに配位した配位子であり;
環Aおよび環Bは各々、5〜6員の芳香族環であり、ここでA−Bは、環A上の窒素原子および環B上のsp2混成炭素原子を介して前記イリジウムに配位した芳香族環の結合された一対を表わし、
前記イリジウム錯体の変数「n」が1〜3の整数値を有し;
環AのXが炭素または窒素原子であり;
Pが、1〜5の整数値を有する変数「a」を伴う重合性基であり、
Sが、アルキレン、ヘテロアルキレン、アリーレン、ヘテロアリーレン、ボラン、エーテル、エステル、アミン、イミン、アミド、イミド、チオエーテルおよびホスフィンからなる群から各々独立して選択される1つ以上の連結単位(linkage unit)を含むスペーサ基であり;
環AおよびBの各々がR1およびR2の基でそれぞれ任意に置換されていてもよく、ここでR1およびR2の各々が、そのそれぞれの環の任意の位置に配置された1つ以上の独立して選択された置換基を表わし、ここで前記置換基の各々がそのそれぞれの環に縮合または連結されており、前記置換基の各々がアルキル、ヘテロアルキル、アリールおよびヘテロアリールからなる群から独立して選択される。) - 前記イリジウム錯体が、
- 前記ホスト電荷輸送化合物がポリマーである、請求項14に記載の電子デバイス。
- 前記有機層が溶液プロセスにより作製される、請求項13に記載の電子デバイス。
- 有機発光デバイスである、請求項13に記載の電子デバイス。
- (a)反応性官能基を有する導電ドーパントと(b)架橋性官能基を有するホスト電荷輸送化合物との溶液混合物を準備するステップ;
第1の電極上に前記溶液混合物を付着させるステップ;
前記ホスト電荷輸送化合物に前記導電ドーパントを架橋させて有機層を形成させるステップ;及び
前記有機層上に第2の電極を付着させるステップ;
を含む、電子デバイスの製造方法。 - 前記架橋ステップが、前記付着させた溶液混合物を加熱するステップを含む、請求項25に記載の方法。
- 前記有機層が正孔注入層である、請求項25に記載の方法。
- 前記溶液混合物を付着させる前記ステップが溶液プロセスにより実施される、請求項25に記載の方法。
- 前記導電ドーパントが、前記ホスト電荷輸送化合物から電子を受容できる電子受容体である、請求項25に記載の方法。
- 前記導電ドーパントのLUMOエネルギー準位が前記ホスト電荷輸送化合物のイオン化ポテンシャルより大きい、請求項29に記載の方法。
- 前記電子デバイスが有機発光デバイスである、請求項25に記載の方法。
- 下記式を有するイオン性化合物。
Ar1、Ar2、Ar3およびAr4は各々互いに独立してアリール基またはヘテロアリール基であり;
Ar1、Ar2、Ar3およびAr4の少なくとも1つが、ビニル、アクリレート、エポキシド、オキセタン、ノルボルネン、トリフルオロエチレン、ベンゾシクロブテン、シロキサン、マレイミド、シアン酸エステル、エチニル、ナジミド、フェニルエチニル、ビフェニレン、フタロニトリル、またはボロン酸と反応できる反応性官能基を有し;
X3がNまたはPであり;
Zn−が、対アニオンであり、「n」はこの対アニオンのイオン価である。)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11420989B2 (en) | 2017-03-06 | 2022-08-23 | Lomox Limited | Cross-linkable organometallic light emitting ligands and complexes |
KR102547153B1 (ko) * | 2022-03-04 | 2023-06-26 | 한양대학교 산학협력단 | 유기 발광 복합체 및 이를 포함하는 유기 발광 박막의 패터닝 방법, 이를 포함하는 유기 발광 조성물, 이를 포함하는 유기 발광 소자 |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8174000B2 (en) * | 2009-02-11 | 2012-05-08 | Universal Display Corporation | Liquid compositions for inkjet printing of organic layers or other uses |
EP2569347A1 (en) | 2010-05-11 | 2013-03-20 | Plextronics, Inc. | Doping conjugated polymers and devices |
US20120049168A1 (en) * | 2010-08-31 | 2012-03-01 | Universal Display Corporation | Cross-Linked Charge Transport Layer Containing an Additive Compound |
WO2012126566A1 (en) * | 2011-03-24 | 2012-09-27 | Merck Patent Gmbh | Organic ionic functional materials |
CN103781845B (zh) | 2011-07-05 | 2016-07-13 | 索尔维美国有限公司 | 垂直相分离半导体有机材料层 |
EP2543671A1 (de) * | 2011-07-08 | 2013-01-09 | cynora GmbH | Querverknüpfung und Stabilisierung von organischen Metallkomplexen in Netzwerken |
JP6269489B2 (ja) | 2011-10-04 | 2018-01-31 | 日産化学工業株式会社 | 正孔注入層および輸送層のための改善されたドーピング法 |
JP6119171B2 (ja) * | 2012-10-05 | 2017-04-26 | 三菱化学株式会社 | イリジウム錯体化合物、該化合物及び溶剤を含有する組成物、該化合物を含有する有機電界発光素子、表示装置及び照明装置 |
CA2939263C (en) * | 2014-02-10 | 2024-01-09 | Timothy P. Bender | Organic light emitting diode device comprising boron subphthalocyanine |
JP6264143B2 (ja) * | 2014-03-27 | 2018-01-24 | 三菱ケミカル株式会社 | イリジウム錯体化合物、該化合物を含む組成物、有機電界発光素子、表示装置及び照明装置 |
WO2016026123A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Compositions comprising oxygen substituted benzocyclobutenes and dienophiles, and electronic devices containing same |
US10297755B2 (en) | 2014-08-21 | 2019-05-21 | Dow Global Technologies Llc | Oxygen substituted benzoclobutenes derived compositions for electronic devices |
WO2016026122A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Benzocyclobutenes derived compositions, and electronic devices containing the same |
EP3434682B1 (en) | 2016-03-24 | 2021-02-24 | Mitsubishi Chemical Corporation | Electron-accepting compound, composition for charge transport film, and light-emitting element using same |
JP6943241B2 (ja) * | 2016-06-24 | 2021-09-29 | 住友化学株式会社 | 発光素子 |
US10062860B2 (en) * | 2016-07-20 | 2018-08-28 | Joled Inc. | Organic electroluminescence device, organic electroluminescence unit, and electronic apparatus |
KR102143264B1 (ko) * | 2016-11-25 | 2020-08-10 | 주식회사 엘지화학 | 아민계 화합물, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
US11196009B2 (en) | 2016-11-25 | 2021-12-07 | Lg Chem, Ltd. | Fluorene derivative, organic light emitting device using same, and manufacturing method therefor |
KR102101058B1 (ko) * | 2016-11-25 | 2020-04-14 | 주식회사 엘지화학 | 플루오렌 유도체, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
KR101999708B1 (ko) | 2016-11-25 | 2019-07-12 | 주식회사 엘지화학 | 이온성 화합물, 이를 포함하는 코팅 조성물 및 유기 발광 소자 |
CN106611823B (zh) * | 2017-01-19 | 2018-07-10 | 江西冠能光电材料有限公司 | 一种可交联有机半导体主体材料及其有机发光二极管应用 |
KR102130880B1 (ko) * | 2017-03-07 | 2020-07-06 | 주식회사 엘지화학 | 화합물, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
KR102123720B1 (ko) * | 2017-03-07 | 2020-06-16 | 주식회사 엘지화학 | 코팅 조성물, 이를 이용하여 제조된 유기 발광 소자 및 이의 제조방법 |
KR102133626B1 (ko) * | 2017-03-07 | 2020-07-13 | 주식회사 엘지화학 | 코팅 조성물, 이를 이용하여 제조된 유기 발광 소자 및 이의 제조방법 |
KR102206819B1 (ko) * | 2018-05-14 | 2021-01-22 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006233162A (ja) * | 2004-03-11 | 2006-09-07 | Mitsubishi Chemicals Corp | 電荷輸送膜用組成物及びイオン化合物、それを用いた電荷輸送膜及び有機電界発光素子、並びに、有機電界発光素子の製造方法及び電荷輸送膜の製造方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3902114A1 (de) | 1989-01-25 | 1990-08-02 | Basf Ag | Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare sulfoniumsalze und verfahren zu deren herstellung |
US5093698A (en) | 1991-02-12 | 1992-03-03 | Kabushiki Kaisha Toshiba | Organic electroluminescent device |
US5120884A (en) * | 1991-02-14 | 1992-06-09 | The Dow Chemical Company | Preparation of hydroxy arylcyclobutenes |
JP3249297B2 (ja) | 1994-07-14 | 2002-01-21 | 三洋電機株式会社 | 有機電界発光素子 |
US5929194A (en) | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
US5773130A (en) | 1996-06-06 | 1998-06-30 | Motorola, Inc. | Multi-color organic electroluminescent device |
JP2000196140A (ja) | 1998-12-28 | 2000-07-14 | Sharp Corp | 有機エレクトロルミネッセンス素子とその製造法 |
WO2000060612A1 (en) * | 1999-04-06 | 2000-10-12 | Cambridge Display Technology Limited | Method for doping a polymer |
KR100320773B1 (ko) | 1999-05-31 | 2002-01-17 | 윤종용 | 포토레지스트 조성물 |
DE10058578C2 (de) | 2000-11-20 | 2002-11-28 | Univ Dresden Tech | Lichtemittierendes Bauelement mit organischen Schichten |
WO2003006468A2 (en) | 2001-07-09 | 2003-01-23 | Merck Patent Gmbh | Polymerisable charge transport compounds |
AU2002323418A1 (en) | 2002-04-08 | 2003-10-27 | The University Of Southern California | Doped organic carrier transport materials |
ATE328050T1 (de) | 2002-04-24 | 2006-06-15 | Merck Patent Gmbh | Reaktive mesogene benzodithiophene |
DE10357044A1 (de) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
EP2325191A1 (en) | 2004-03-11 | 2011-05-25 | Mitsubishi Chemical Corporation | Composition for charge-transporting film and ion compound, charge-transporting film and organic electroluminescent device using same |
KR100637450B1 (ko) * | 2005-02-16 | 2006-10-23 | 한양대학교 산학협력단 | 플루오로알킬술폰늄염의 광산발생기가 치환된 화합물과 이를 중합한 공중합체 |
US7678528B2 (en) * | 2005-11-16 | 2010-03-16 | Az Electronic Materials Usa Corp. | Photoactive compounds |
JP5148090B2 (ja) | 2005-11-16 | 2013-02-20 | 信越化学工業株式会社 | レジスト材料及びこれを用いたパターン形成方法 |
US7629106B2 (en) | 2005-11-16 | 2009-12-08 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process using the same |
EP1968131A4 (en) | 2005-12-27 | 2009-08-19 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENT DEVICE AND MATERIAL THEREFOR |
JP5100115B2 (ja) | 2006-03-16 | 2012-12-19 | 東洋合成工業株式会社 | スルホニウム塩及び酸発生剤 |
EP2125713B1 (en) * | 2006-10-04 | 2012-04-18 | Basf Se | Sulphonium salt photoinitiators |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
-
2009
- 2009-05-08 EP EP09770604A patent/EP2291872A1/en not_active Withdrawn
- 2009-05-08 WO PCT/US2009/043255 patent/WO2009158069A1/en active Application Filing
- 2009-05-08 KR KR1020107029294A patent/KR101618896B1/ko active IP Right Grant
- 2009-05-08 JP JP2011516363A patent/JP2011525918A/ja not_active Withdrawn
- 2009-05-08 US US12/996,952 patent/US9184394B2/en active Active
- 2009-05-08 CN CN200980124300.8A patent/CN102077381B/zh active Active
-
2014
- 2014-04-30 JP JP2014093435A patent/JP5878585B2/ja active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006233162A (ja) * | 2004-03-11 | 2006-09-07 | Mitsubishi Chemicals Corp | 電荷輸送膜用組成物及びイオン化合物、それを用いた電荷輸送膜及び有機電界発光素子、並びに、有機電界発光素子の製造方法及び電荷輸送膜の製造方法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11420989B2 (en) | 2017-03-06 | 2022-08-23 | Lomox Limited | Cross-linkable organometallic light emitting ligands and complexes |
KR102547153B1 (ko) * | 2022-03-04 | 2023-06-26 | 한양대학교 산학협력단 | 유기 발광 복합체 및 이를 포함하는 유기 발광 박막의 패터닝 방법, 이를 포함하는 유기 발광 조성물, 이를 포함하는 유기 발광 소자 |
WO2023167521A1 (ko) * | 2022-03-04 | 2023-09-07 | 한양대학교 산학협력단 | 유기 발광 복합체 및 이를 포함하는 유기 발광 박막의 패터닝 방법, 이를 포함하는 유기 발광 조성물, 이를 포함하는 유기 발광 소자 |
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Publication number | Publication date |
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EP2291872A1 (en) | 2011-03-09 |
CN102077381B (zh) | 2014-10-22 |
JP5878585B2 (ja) | 2016-03-08 |
KR101618896B1 (ko) | 2016-05-09 |
WO2009158069A1 (en) | 2009-12-30 |
US9184394B2 (en) | 2015-11-10 |
JP2011525918A (ja) | 2011-09-29 |
KR20110037972A (ko) | 2011-04-13 |
US20110089411A1 (en) | 2011-04-21 |
CN102077381A (zh) | 2011-05-25 |
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